Pyridine → 2-Nitrobenzoyl chloride

HRID 651429Notes

Reaction equation

HRID 651429 reaction equation
[Cl:1]C1C=C(CO)C=C(Cl)N=1.N1C=CC=CC=1.[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](O)=[O:23])([O-:19])=[O:18].S(Cl)(Cl)=O>ClCCl>[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([Cl:1])=[O:23])([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 110872-Nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Product 1

HCID 118752-Nitrobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.4 g of 2,6-dichloro-4-pyridinemethanol were dissolved into 5 ml of pyridine, and the solution was cooled by ice. To this, 1.5 g of 2-nitrobenzoyl chloride, which was prepared from 2-nitrobenzoic acid and thionyl chloride, were added dropwise. After the reacted solution was stirred for 2 hours, dichloromethane was added. The organic phase was washed with water, and was dried by adding sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography to obtain 1.4 g of (2,6-dichloro-4-pyridinyl)methyl 2-nitrobenzoate ester (Compound No. 69).

Workup

  1. temperaturethe solution was cooled by ice
  2. additionwere added dropwise
  3. washThe organic phase was washed with water
  4. customwas dried
  5. additionby adding sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6fbf19ffc48248c1be633803a49b6825
Source dataset
uspto-grants-2001_08
Patent number
US06281231B1

Reaction notes

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